5-Hydr-oxy-1-(3-hydr-oxy-2-naphtho-yl)-3,5-dimethyl-2-pyrazoline.

In the title mol-ecule, C(16)H(16)N(2)O(3), intra-molecular O-H⋯O hydrogen bonds influence the mol-ecular conformation. Inter-molecular O-H⋯O hydrogen bonds [O⋯O = 2.922 (2) Å] link the mol-ecules into centrosymmetric dimers. Weak inter-molecular C-H⋯O inter-actions assemble these dimers into layers parallel to the bc plane.

Related literature

A highly puckered 60-membered metalladiaza­macrocycle was reported by Moon et al. (2006 ▶), and two manganese metallacrowns with the ligand N-acyl-3-hydr­oxy-2-naphthalene­carbohydrazide were reported by Dou et al. (2006 ▶). The ligand 1-benzoyl-3,5-dimethyl-5-(1-benzoyl­hydrazido)pyrazoline was first synthesized by Mukhopadhyay & Pal (2004 ▶).

Experimental

Crystal data

C16H16N2O3

M = 284.31

Monoclinic,

a = 12.368 (6) Å

b = 7.428 (4) Å

c = 17.041 (9) Å

β = 109.331 (7)°

V = 1477.3 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.64 × 0.57 × 0.39 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.945, T max = 0.966

7363 measured reflections

2588 independent reflections

1627 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.00

2588 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023027/cv2430sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023027/cv2430Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H16N2O3	F000 = 600
Mr = 284.31	Dx = 1.278 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 12.368 (6) Å	Cell parameters from 2043 reflections
b = 7.428 (4) Å	θ = 2.5–23.0º
c = 17.041 (9) Å	µ = 0.09 mm−1
β = 109.331 (7)º	T = 298 (2) K
V = 1477.3 (13) Å3	Block, yellow
Z = 4	0.64 × 0.57 × 0.39 mm

Bruker SMART 1000 CCD area-detector diffractometer	2588 independent reflections
Radiation source: fine-focus sealed tube	1627 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.042
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→14
Tmin = 0.945, Tmax = 0.966	k = −8→8
7363 measured reflections	l = −20→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0553P)2 + 0.3243P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2588 reflections	Δρmax = 0.15 e Å−3
190 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	−0.04413 (13)	0.2580 (2)	0.17142 (9)	0.0490 (5)
N2	−0.01893 (14)	0.2214 (2)	0.25642 (10)	0.0518 (5)
O1	−0.00569 (12)	0.2318 (2)	0.05376 (8)	0.0685 (5)
O2	0.18079 (13)	0.1067 (2)	0.04814 (9)	0.0751 (5)
H2	0.1117	0.1265	0.0322	0.113*
O3	−0.21475 (12)	0.1233 (2)	0.08086 (9)	0.0660 (5)
H3	−0.1868	0.1116	0.0437	0.099*
C1	0.03222 (17)	0.2371 (3)	0.13121 (12)	0.0492 (5)
C2	0.15776 (16)	0.2220 (3)	0.17539 (12)	0.0459 (5)
C3	0.22724 (19)	0.1534 (3)	0.12957 (13)	0.0547 (6)
C4	0.34226 (19)	0.1307 (3)	0.16761 (15)	0.0650 (6)
H4	0.3857	0.0837	0.1372	0.078*
C5	0.39654 (18)	0.1758 (3)	0.25100 (15)	0.0585 (6)
C6	0.5152 (2)	0.1459 (4)	0.29304 (19)	0.0809 (8)
H6	0.5599	0.0937	0.2648	0.097*
C7	0.5633 (2)	0.1923 (4)	0.3733 (2)	0.0918 (9)
H7	0.6409	0.1707	0.3998	0.110*
C8	0.4998 (2)	0.2720 (4)	0.41801 (17)	0.0803 (8)
H8	0.5351	0.3034	0.4735	0.096*
C9	0.38560 (18)	0.3038 (3)	0.38005 (14)	0.0639 (6)
H9	0.3434	0.3579	0.4097	0.077*
C10	0.33104 (16)	0.2550 (3)	0.29614 (13)	0.0510 (5)
C11	0.21191 (16)	0.2757 (3)	0.25610 (12)	0.0478 (5)
H11	0.1685	0.3277	0.2854	0.057*
C12	−0.19627 (19)	0.4480 (3)	0.07493 (14)	0.0704 (7)
H12A	−0.1643	0.5503	0.1092	0.106*
H12B	−0.2778	0.4624	0.0510	0.106*
H12C	−0.1634	0.4385	0.0314	0.106*
C13	−0.17009 (16)	0.2794 (3)	0.12726 (12)	0.0512 (5)
C14	−0.21392 (17)	0.2823 (3)	0.20069 (12)	0.0561 (6)
H14A	−0.2422	0.4008	0.2078	0.067*
H14B	−0.2750	0.1952	0.1932	0.067*
C15	−0.11177 (18)	0.2339 (3)	0.27323 (12)	0.0503 (5)
C16	−0.1148 (2)	0.2027 (4)	0.35844 (13)	0.0700 (7)
H16A	−0.0392	0.1736	0.3948	0.105*
H16B	−0.1658	0.1048	0.3576	0.105*
H16C	−0.1413	0.3096	0.3780	0.105*

	U11	U22	U33	U12	U13	U23
N1	0.0456 (9)	0.0637 (12)	0.0350 (9)	0.0036 (8)	0.0099 (7)	−0.0026 (8)
N2	0.0550 (10)	0.0632 (12)	0.0363 (9)	0.0032 (9)	0.0139 (8)	−0.0016 (8)
O1	0.0661 (10)	0.1004 (14)	0.0375 (9)	0.0037 (9)	0.0149 (7)	−0.0036 (8)
O2	0.0795 (11)	0.0951 (13)	0.0596 (10)	−0.0029 (10)	0.0349 (8)	−0.0186 (9)
O3	0.0613 (9)	0.0802 (12)	0.0583 (9)	−0.0128 (8)	0.0220 (7)	−0.0254 (8)
C1	0.0543 (12)	0.0527 (13)	0.0402 (12)	−0.0009 (10)	0.0149 (10)	−0.0026 (10)
C2	0.0477 (11)	0.0455 (12)	0.0458 (12)	−0.0003 (9)	0.0172 (9)	0.0000 (9)
C3	0.0618 (14)	0.0525 (14)	0.0552 (14)	−0.0047 (11)	0.0264 (11)	−0.0050 (11)
C4	0.0583 (14)	0.0659 (16)	0.0843 (18)	0.0027 (12)	0.0418 (13)	−0.0087 (13)
C5	0.0487 (12)	0.0512 (14)	0.0780 (16)	−0.0018 (10)	0.0241 (11)	0.0009 (12)
C6	0.0516 (15)	0.083 (2)	0.111 (2)	0.0078 (13)	0.0310 (15)	−0.0011 (17)
C7	0.0461 (14)	0.110 (2)	0.109 (2)	0.0047 (15)	0.0115 (16)	0.006 (2)
C8	0.0534 (15)	0.092 (2)	0.0789 (18)	−0.0047 (14)	0.0001 (13)	0.0033 (15)
C9	0.0519 (13)	0.0683 (16)	0.0643 (15)	−0.0033 (11)	0.0095 (11)	−0.0032 (12)
C10	0.0463 (12)	0.0437 (13)	0.0617 (14)	−0.0021 (9)	0.0159 (10)	0.0017 (10)
C11	0.0467 (11)	0.0460 (12)	0.0518 (12)	0.0014 (9)	0.0177 (9)	−0.0011 (10)
C12	0.0645 (14)	0.0791 (18)	0.0578 (14)	0.0139 (13)	0.0072 (11)	0.0067 (13)
C13	0.0442 (11)	0.0611 (14)	0.0422 (12)	0.0014 (10)	0.0059 (9)	−0.0105 (10)
C14	0.0513 (12)	0.0642 (15)	0.0525 (13)	0.0044 (10)	0.0169 (10)	−0.0115 (11)
C15	0.0556 (13)	0.0515 (13)	0.0450 (12)	0.0024 (10)	0.0184 (10)	−0.0088 (10)
C16	0.0845 (17)	0.0810 (18)	0.0526 (14)	0.0132 (14)	0.0337 (12)	−0.0003 (12)

N1—C1	1.347 (3)	C7—C8	1.393 (4)
N1—N2	1.404 (2)	C7—H7	0.9300
N1—C13	1.497 (3)	C8—C9	1.366 (3)
N2—C15	1.276 (3)	C8—H8	0.9300
O1—C1	1.246 (2)	C9—C10	1.412 (3)
O2—C3	1.360 (2)	C9—H9	0.9300
O2—H2	0.8200	C10—C11	1.412 (3)
O3—C13	1.409 (2)	C11—H11	0.9300
O3—H3	0.8200	C12—C13	1.509 (3)
C1—O1	1.246 (2)	C12—H12A	0.9600
C1—C2	1.489 (3)	C12—H12B	0.9600
C2—C11	1.375 (3)	C12—H12C	0.9600
C2—C3	1.432 (3)	C13—C14	1.520 (3)
C3—C4	1.365 (3)	C14—C15	1.490 (3)
C4—C5	1.397 (3)	C14—H14A	0.9700
C4—H4	0.9300	C14—H14B	0.9700
C5—C10	1.416 (3)	C15—C16	1.483 (3)
C5—C6	1.421 (3)	C16—H16A	0.9600
C6—C7	1.344 (4)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C1—N1—N2	123.32 (16)	C9—C10—C11	122.3 (2)
C1—N1—C13	122.99 (16)	C9—C10—C5	119.29 (19)
N2—N1—C13	112.21 (15)	C11—C10—C5	118.4 (2)
C15—N2—N1	107.99 (16)	C2—C11—C10	122.45 (19)
C3—O2—H2	109.5	C2—C11—H11	118.8
C13—O3—H3	109.5	C10—C11—H11	118.8
O1—C1—N1	117.46 (18)	C13—C12—H12A	109.5
O1—C1—C2	119.79 (18)	C13—C12—H12B	109.5
N1—C1—C2	122.75 (17)	H12A—C12—H12B	109.5
C11—C2—C3	117.85 (18)	C13—C12—H12C	109.5
C11—C2—C1	124.41 (18)	H12A—C12—H12C	109.5
C3—C2—C1	117.69 (18)	H12B—C12—H12C	109.5
O2—C3—C4	118.35 (19)	O3—C13—N1	110.11 (16)
O2—C3—C2	121.35 (19)	O3—C13—C12	112.56 (17)
C4—C3—C2	120.3 (2)	N1—C13—C12	111.68 (18)
C3—C4—C5	121.9 (2)	O3—C13—C14	107.04 (18)
C3—C4—H4	119.1	N1—C13—C14	100.54 (15)
C5—C4—H4	119.1	C12—C13—C14	114.20 (19)
C4—C5—C10	118.92 (19)	C15—C14—C13	104.14 (17)
C4—C5—C6	122.9 (2)	C15—C14—H14A	110.9
C10—C5—C6	118.1 (2)	C13—C14—H14A	110.9
C7—C6—C5	120.6 (2)	C15—C14—H14B	110.9
C7—C6—H6	119.7	C13—C14—H14B	110.9
C5—C6—H6	119.7	H14A—C14—H14B	108.9
C6—C7—C8	121.7 (2)	N2—C15—C16	121.66 (19)
C6—C7—H7	119.1	N2—C15—C14	114.22 (18)
C8—C7—H7	119.1	C16—C15—C14	124.1 (2)
C9—C8—C7	119.7 (3)	C15—C16—H16A	109.5
C9—C8—H8	120.1	C15—C16—H16B	109.5
C7—C8—H8	120.1	H16A—C16—H16B	109.5
C8—C9—C10	120.5 (2)	C15—C16—H16C	109.5
C8—C9—H9	119.7	H16A—C16—H16C	109.5
C10—C9—H9	119.7	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.79	2.518 (2)	147
O3—H3···O1	0.82	2.36	2.888 (2)	122
O3—H3···O2i	0.82	2.27	2.922 (2)	137
C9—H9···O3ii	0.93	2.57	3.388 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.79	2.518 (2)	147
O3—H3⋯O1	0.82	2.36	2.888 (2)	122
O3—H3⋯O2i	0.82	2.27	2.922 (2)	137
C9—H9⋯O3ii	0.93	2.57	3.388 (3)	147

Symmetry codes: (i) ; (ii) .